Luv Doc: A Taste for Ballin'

Dear Luv Doc,

After two years with my boyfriend, I have come to the inescapable conclusion that he is cheap. Yes, he has lots of other nice qualities, but when it comes to money, he really hates to let go of it. We always split dinner bills and buy our own movie/concert tickets. He will drive/walk forever so he doesn't have to pay for parking. He tries to get out of tipping whenever he can, and when he does tip, it's never more than 15%. He would rather stay home and "Netflix and chill" than go out. He only buys clothes if they are on sale. And, he never buys me gifts. Look, I am not a greedy person, but all his penny-pinching can get really exhausting at times. The crazy thing is that he has a good job – he's a CPA – so it's not like he doesn't make good money. How do I get him to loosen up?

– The Future Ms. Miser

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You have a solid gripe, Ms. Miser, but I feel it's important to point out that you knowingly entered into a relationship with a bean counter. It's literally his job to keep track of money. That's what he does all day. I don't think it's reasonable to expect him to clock out and instantly turn into a blinged-out baller (A shot-caller? With 20-inch blades on his Impala?). Nope. Not gonna happen. But wait! Before you absolutely give up your fantasy of seeing "diamond grills in his grin," might I suggest a few things you could try?

Certain mental health professionals claim that when people are stingy, it's because they feel a lack of control in other areas of their lives. Keeping a tight rein on their finances gives them a feeling of security. Hey! That's not so bad! Better than some batty, neurotic fear that aliens are reading their thoughts. I mean, we can all (OK, apparently 99% of us) relate to the fear of not having any money. That's some real shit. Everybody has fears: Howard Hughes feared he was going to die. To his credit, that motherfucker was spot-on.

Fear becomes a problem when it unduly affects your quality of life. For instance, when you become a germophobe like Howard Hughes and walk around the house with Kleenex boxes on your feet ... and refuse to cut your fingernails or hair more than once a year. I mean, the long hair might be pretty dope, but you know those fingernails are going to earn you a permanent seat on the crazy couch.

So I think the place to start with your boyfriend is to work on his insecurities. I don't mean to tease him about them – unless you're an Irish Catholic and can't show affection in any other way. I mean to make him feel secure however you're willing. You might also experiment with trying to get him to spend money on himself, but not on things. Things can be readily monetized. No, get him to spend money on experiences. Get him to spend money on making himself make other people happy (tipping!). Burn through a bottle of expensive wine. Get a VIP pass to ACL. Rent a stretch limo. Make it rain ... dollar bills ... no, hundies! OK, I'm getting a little ahead of myself, but you get the idea. Be careful, though: Once he gets a taste for ballin', it might be hard to rein him in.